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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2022-03-07 02:51:36 UTC
HMDB IDHMDB0014382
Secondary Accession Numbers
  • HMDB14382
Metabolite Identification
Common NameButabarbital
DescriptionButabarbital (trade name Butisol) is a prescription barbiturate sleep aid. Butabarbital has a particularly fast onset of effects and short duration of action compared to other barbiturates, which makes it useful for certain applications such as treating severe insomnia and relieving anxiety before surgical procedures; however it is also relatively dangerous particularly when combined with alcohol, and so is now rarely used, although it is still prescribed in some Eastern European and South American countries. Its short duration of action gives butabarbital a high abuse potential, comparable to secobarbital. [Wikipedia ]
Structure
Data?1582753172
Synonyms
ValueSource
5-Ethyl-5-(1-methylpropyl)-2,4,6(1H,3H,5H)-pyrimidinetrioneChEBI
5-Ethyl-5-(1-methylpropyl)barbituric acidChEBI
5-Sec-butyl-5-ethyl-2,4,6(1H,3H,5H)-pyrimidinetrioneChEBI
5-Sec-butyl-5-ethylbarbituric acidChEBI
5-Sec-butyl-5-ethylpyrimidine-2,4,6(1H,3H,5H)-trioneChEBI
ButisolChEBI
SecbutabarbitalChEBI
5-Ethyl-5-(1-methylpropyl)barbitateGenerator
5-Ethyl-5-(1-methylpropyl)barbitic acidGenerator
5-Sec-butyl-5-ethylbarbitateGenerator
5-Sec-butyl-5-ethylbarbitic acidGenerator
ButabarbitoneHMDB
ButrateHMDB
SecbubarbitalHMDB
SecbutobarbitalHMDB
SecbutobarbitoneHMDB
Sodium butabarbitalHMDB
SecumalumHMDB
2,4,6(1H,3H,5H)-Pyrimidinetrione, 5-ethyl-5-(1-methylpropyl)-, monosodium saltHMDB
Butisol sodiumHMDB
Wallace brand OF butabarbital sodiumHMDB
Butabarbital sodiumHMDB
Secbutabarbital sodiumHMDB
Halsey drug brand OF butabarbital sodiumHMDB
SarisolHMDB
Chemical FormulaC10H16N2O3
Average Molecular Weight212.2456
Monoisotopic Molecular Weight212.116092388
IUPAC Name5-(butan-2-yl)-5-ethyl-1,3-diazinane-2,4,6-trione
Traditional Namebutabarbital
CAS Registry Number125-40-6
SMILES
CCC(C)C1(CC)C(=O)NC(=O)NC1=O
InChI Identifier
InChI=1S/C10H16N2O3/c1-4-6(3)10(5-2)7(13)11-9(15)12-8(10)14/h6H,4-5H2,1-3H3,(H2,11,12,13,14,15)
InChI KeyZRIHAIZYIMGOAB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as barbituric acid derivatives. Barbituric acid derivatives are compounds containing a perhydropyrimidine ring substituted at C-2, -4 and -6 by oxo groups.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentBarbituric acid derivatives
Alternative Parents
Substituents
  • Barbiturate
  • N-acyl urea
  • Ureide
  • 1,3-diazinane
  • Dicarboximide
  • Urea
  • Carbonic acid derivative
  • Carboxylic acid derivative
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point166.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.39 g/LNot Available
LogP1.5Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.39 g/LALOGPS
logP1.7ALOGPS
logP1.45ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)8.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.27 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity53.4 m³·mol⁻¹ChemAxon
Polarizability21.41 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+150.43631661259
DarkChem[M-H]-145.88131661259
DeepCCS[M+H]+147.80230932474
DeepCCS[M-H]-144.19730932474
DeepCCS[M-2H]-181.39730932474
DeepCCS[M+Na]+156.93630932474
AllCCS[M+H]+147.432859911
AllCCS[M+H-H2O]+143.532859911
AllCCS[M+NH4]+151.032859911
AllCCS[M+Na]+152.132859911
AllCCS[M-H]-149.432859911
AllCCS[M+Na-2H]-150.232859911
AllCCS[M+HCOO]-151.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ButabarbitalCCC(C)C1(CC)C(=O)NC(=O)NC1=O2856.1Standard polar33892256
ButabarbitalCCC(C)C1(CC)C(=O)NC(=O)NC1=O1641.4Standard non polar33892256
ButabarbitalCCC(C)C1(CC)C(=O)NC(=O)NC1=O1642.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Butabarbital,1TMS,isomer #1CCC(C)C1(CC)C(=O)NC(=O)N([Si](C)(C)C)C1=O1648.0Semi standard non polar33892256
Butabarbital,1TMS,isomer #1CCC(C)C1(CC)C(=O)NC(=O)N([Si](C)(C)C)C1=O1814.2Standard non polar33892256
Butabarbital,1TMS,isomer #1CCC(C)C1(CC)C(=O)NC(=O)N([Si](C)(C)C)C1=O2650.2Standard polar33892256
Butabarbital,2TMS,isomer #1CCC(C)C1(CC)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O1631.3Semi standard non polar33892256
Butabarbital,2TMS,isomer #1CCC(C)C1(CC)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O1851.6Standard non polar33892256
Butabarbital,2TMS,isomer #1CCC(C)C1(CC)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O2201.5Standard polar33892256
Butabarbital,1TBDMS,isomer #1CCC(C)C1(CC)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O1856.5Semi standard non polar33892256
Butabarbital,1TBDMS,isomer #1CCC(C)C1(CC)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O2049.8Standard non polar33892256
Butabarbital,1TBDMS,isomer #1CCC(C)C1(CC)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O2686.1Standard polar33892256
Butabarbital,2TBDMS,isomer #1CCC(C)C1(CC)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2042.4Semi standard non polar33892256
Butabarbital,2TBDMS,isomer #1CCC(C)C1(CC)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2297.2Standard non polar33892256
Butabarbital,2TBDMS,isomer #1CCC(C)C1(CC)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O2357.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Butabarbital GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a7i-8900000000-fc5f17ec8979e31b77ac2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Butabarbital GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a4l-6900000000-6e0cbc3d26c5541ad8eb2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butabarbital 10V, Positive-QTOFsplash10-03di-1290000000-73748d3c96bdcbc7692d2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butabarbital 20V, Positive-QTOFsplash10-0007-3900000000-c62b6d06318be5ee7a262016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butabarbital 40V, Positive-QTOFsplash10-0a4i-9000000000-d815b39070a4a2b620ee2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butabarbital 10V, Negative-QTOFsplash10-0296-8950000000-e8d3b0ea461e5ad690682016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butabarbital 20V, Negative-QTOFsplash10-0006-9500000000-43d75b9170cae3f239fa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butabarbital 40V, Negative-QTOFsplash10-000x-9400000000-ec7399384bd48aaa6ee42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butabarbital 10V, Positive-QTOFsplash10-0a4i-0900000000-121a04bb64c32af4a00f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butabarbital 20V, Positive-QTOFsplash10-0a4i-3900000000-58caeb294d4571a30cf42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butabarbital 40V, Positive-QTOFsplash10-0002-9300000000-527f2d60d78505d849532021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butabarbital 10V, Negative-QTOFsplash10-03di-1290000000-994157d74b9e27e50e2d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butabarbital 20V, Negative-QTOFsplash10-0006-9000000000-90726b17dc36e29c52992021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Butabarbital 40V, Negative-QTOFsplash10-0006-9100000000-85bbea89298999fca7c32021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00237 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00237 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00237
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2385
KEGG Compound IDC07827
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkButabarbital
METLIN IDNot Available
PubChem Compound2479
PDB IDNot Available
ChEBI ID3228
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in ionotropic glutamate receptor activity
Specific function:
Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L- glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist. May be involved in the transmission of light information from the retina to the hypothalamus. Modulates cell surface expression of NETO2
Gene Name:
GRIK2
Uniprot ID:
Q13002
Molecular weight:
102582.5
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]
  2. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207 ]
General function:
Involved in ionotropic glutamate receptor activity
Specific function:
Ionotropic glutamate receptor. L-glutamate acts as an excitatory neurotransmitter at many synapses in the central nervous system. Binding of the excitatory neurotransmitter L- glutamate induces a conformation change, leading to the opening of the cation channel, and thereby converts the chemical signal to an electrical impulse. The receptor then desensitizes rapidly and enters a transient inactive state, characterized by the presence of bound agonist
Gene Name:
GRIA2
Uniprot ID:
P42262
Molecular weight:
98820.3
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]
  2. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA1
Uniprot ID:
P14867
Molecular weight:
51801.4
References
  1. Whiting PJ: The GABAA receptor gene family: new opportunities for drug development. Curr Opin Drug Discov Devel. 2003 Sep;6(5):648-57. [PubMed:14579514 ]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
  3. Krasowski MD, Harrison NL: General anaesthetic actions on ligand-gated ion channels. Cell Mol Life Sci. 1999 Aug 15;55(10):1278-303. [PubMed:10487207 ]
  4. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  6. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  7. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA2
Uniprot ID:
P47869
Molecular weight:
51325.9
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA3
Uniprot ID:
P34903
Molecular weight:
55164.1
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA4
Uniprot ID:
P48169
Molecular weight:
61622.6
References
  1. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA5
Uniprot ID:
P31644
Molecular weight:
52145.6
References
  1. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]
  2. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
General function:
Involved in ion transport
Specific function:
GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel
Gene Name:
GABRA6
Uniprot ID:
Q16445
Molecular weight:
51023.7
References
  1. Mehta AK, Ticku MK: An update on GABAA receptors. Brain Res Brain Res Rev. 1999 Apr;29(2-3):196-217. [PubMed:10209232 ]
  2. Yamakura T, Bertaccini E, Trudell JR, Harris RA: Anesthetics and ion channels: molecular models and sites of action. Annu Rev Pharmacol Toxicol. 2001;41:23-51. [PubMed:11264449 ]